The University of Western Australia

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Scott Stewart

Dr Scott Stewart

Senior Lecturer
Molecular Sciences, School of

Contact details
Address
School of Molecular Sciences
The University of Western Australia (M313)
35 Stirling Highway
CRAWLEY WA 6009
Australia
Phone
+61 8 6488 3180
Fax
+61 8 6488 1005
Email
scott.stewart@uwa.edu.au
Personal homepage
http://www.scottstewartchemistry.com
Location
Room 330, Bayliss Building, Perth campus
Qualifications
BSc Deakin, PhD ANU
Biography
A/Prof Scott Stewart completed a PhD at the Research School of Chemistry (ANU) and in 2002, A/Prof Stewart was awarded an Alexander von-Humboldt Fellowship to work at the Universität Göttingen, Germany. He was appointed at The University of Western Australia in late 2005. In 2010 A/Prof Stewart was awarded the RACI Athel Beckwith Lectureship and a second Alexander von-Humboldt Fellowship. Recently he has received Fellowship from the Japan Society for the Promotion of Science and the Tasmanian Alkaloids Lectureship.
Key research
Research interests include:
1. The efficient synthesis of natural products and their simplified ring systems.
2. The development of palladium and nickel catalysed cross coupling reactions
3. The use of domino type reactions in organic synthesis
4. The synthesis of new nickel catalysts
5. Medicinal chemistry: antibacterial agents; thalidomide analogues; anti-cancer agents
Publications
57. Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts, J. Am Chem Soc, 2017, DOI 10.1021/jacs.7b06408.


56. T. Miura, T. Nakamuro, S. G. Stewart, Y. Nagata, M. Murakami, Synthesis of Enantiopure C3-Symmetric Triangular Molecules, Angew. Chem. Int. Ed. 2017, 56, 3334 –3338

55. M. W. Shi, S. G. Stewart, A. N. Sobolev, B. Dittrich, T. Schirmeister, P. Luger, M. Hesse, Y-S. Chen, P. R. Spackman, M. A. Spackman, S. Grabowsky, Approaching an experimental electron density model of the biologically active trans-epoxysuccinyl amide group—Substituent effects vs. crystal packing, J. Phys. Org. Chem, 2017, DOI: 10.1002/poc.3683

54. T. Miura, T. Tanaka, Q. Zhao, S. G. Stewart, M. Murakami, Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols, Helvetica Chimica Acta, 2017,

53. K. Woo, S. G. Stewart, G. S Kong, M. L Finch-Edmondson, B. J. Dwyer, S. Y. Yeung, L. J. Abraham, S. S. Kampmann, L. A. Diepeveen, A. M. Passman, C. L. Elsegood, J. E. E. Tirnitz-Parker, B. A. Callus, J. K. Olynyk, G. C. T. Yeoh, George C. T. Identification of a thalidomide derivative that selectively targets tumorigenic liver progenitor cells and comparing its effects with lenalidomide and sorafenib, E J Med Chem, 2016, 120, 275.

52. J. A. Duczynski, R. Fuller, S. G. Stewart, tert-Butyldimethylsilyl Amine (TBDMS-NH2): A Mild and Green Reagent for the Protection of Benzyl Alcohols, Phenols, and Carboxylic Acids under Solvent-Free Conditions. Aust. J. Chem. 2016, 69, 1172–1179.

51. S. S. Kampmann, N. Y. T. Man, A. J. McKinley, G. A. Koutsantonis, S. G. Stewart, Exploring the Catalytic Reactivity of Nickel Phosphine–Phosphite Complexes. Aust. J Chem. 2015, doi.org/10.1071/CH15459.


50. S. S. Kampmann, B. W. Skelton, D. A. Wild, G. A. Koutsantonis, S. G. Stewart, An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C–N Cross-Coupling Reactions. Eur. J. Org. Chem. 2015, 5995–6004.

49. S. S. Kampmann, B. W. Skelton, G. C. Yeoh, L. J Abraham, N. A. Lengkeek, K. A Stubbs, C. H Heath, S. G. Stewart, The synthesis and fluorescence profile of novel thalidomide analogues, Tetrahedron, 2015, 71, 8140-8149.

48. J. Chen, K. Natte, N. Y.T. Man, S. G. Stewart, X-F Wu, Convenient copper-mediated Chan–Lam coupling of 2-aminopyridine: facile synthesis of N-arylpyridin-2-amines, Tetrahedron Lett. 2015, 56, 4843–4847.

47. N. Y. T Man, W. Li, S. G. Stewart, X-F. Wu, Transition Metal-free Methylation of Amines with Formaldehyde as the Reductant and Methyl Source, CHIMIA International Journal for Chemistry, 2015, 69 (6), 345-347.


46. K. D. Jones, J. E. Rixson, B. W. Skelton, K. M. Gericke, S. G. Stewart, The total synthesis of Heraclemycin B through a b-keto sulfoxide and aldehyde annulation, Asian J. Org. Chem, 2015, 4, 936-942.

45. J. E. Rixson, J. R Abraham, Y. Egoshi, B. W. Skelton, K. Young, J Gilbert, J. A Sakoff, K. M. Gericke, A. McCluskey, S G. Stewart, The Synthesis and Biological Activity of Novel Anthracenone-pyranones and Anthracenone-furans, Bioorg. Med. Chem. 2015, 23, 3552-3565.

44. C. Shen, N. Y. T. Man, S. Stewart, X-F. Wu, Palladium-catalyzed dicarbonylative synthesis of tetracycle quinazolinones, Org. Biomol. Chem, 2015, 13, 4422-4425.

43. S. S. Kampmann; B. W. Skelton; D. A. Wild; G. A. Koutsantonis; S. G. Stewart, Tris(tri-o-tolyl phosphite-κP)nickel: a coordinatively unsaturated nickel(0) complex, Acta Cryst. 2015. C71, 188–190.

42. M. W. Shi, A. N. Sobolev, T. Schirmeister, B. Engels, T. C. Schmidt, P. Luger, S. Mebs, B. Dittrich, Y-S. Chen, J. M. Bak, D. Jayatilaka, C. S. Bond, M. J. Turner, S. G. Stewart, M. A. Spackman, S. Grabowsky, Electrostatic complementarity in pseudoreceptor modeling based on drug molecule crystal structures: the case of loxistatin acid (E64c) New J. Chem., 2015, 39, 1628-1633.

41. S. S. Kampmann; A. N. Sobolev; G. A. Koutsantonis; S. G. Stewart; Stable Nickel(0) Phosphites as Catalysts for C-N cross Coupling Reactions, Advanced Synthesis & Catalysis, 2014, 356, 1967–1973.

40. S. G. Stewart, Modern Domino Reactions Containing a Michael Addition Reaction (Chapter 7) Domino Reactions, Concepts for Efficient Organic Synthesis, Tietze, Lutz F. (Editor) 2014, Wiley-VCH.

39. R. A. Boulos, N. Y. T. Man, N. A. Lengkeek, K. A. Hammer, N. F. Foster, N. A. Stemberger, B. W. Skelton, P. Y Wong, B. Martinac, T. V. Riley, A. J McKinley, S. G Stewart, Inspiration from old dyes: New tris-stilbene compounds as potent Gram-positive anti-bacterial agents. Chem, Eur, J, 2013, 19 (52), 17980-17988.

38. J. E. Rixson, B. W. Skelton, G. A. Koutsantonis, K. M. Gericke, S, G. Stewart, Domino Reactions for the Synthesis of Anthrapyran-2-ones and the Total Synthesis of the Natural Product (±)-BE-26554A; Organic Letters, 2013, 15 (18), 4834–4837.

37. T. Miura, T. Tanaka, K. Hiraga, S. G. Stewart, M. Murakami; Stereoselective Synthesis of 2,3-Dihydropyrroles from Terminal Alkynes, Azides, and α,β-Unsaturated Aldehydes via N-Sulfonyl-1,2,3-triazoles; Journal of the American Chemical Society; 2013, 135 (37), 13652–13655.

36. S. G. Stewart, Intramolecular Heck Reactions-Heterocycle Synthesis, Cross Coupling and Heck-Type Reactions (Chapter 3) Metal-Catalyzed Heck-Type Reactions and C—C Cross Coupling via C—H Activation (Thieme), Science of Synthesis 2013.

35. L. F. Tietze, S. G. Stewart, M. A. Düfert; Domino Reactions in the Enantioselective Synthesis of Bioactive Natural Products (Ch9), Modern Tools for the Synthesis of Complex Bioactive Molecules, Ed Cossy, Janine/ Arseniyadis, Stellios 2013

34. E. Eroglu, X. Chen, M. Bradshaw, V. Agarwal, J. Zou, S. G. Stewart, X. Duan, R. N. Lamb, S. M. Smith, C. L. Raston, K. S. Iyer, Biogenic production of palladium nanocrystals using microalgae and their immobilization on chitosan nanofibers for catalytic applications, RSC Adv, 2013, 3, 1009-1012.

33. D. L. Priebbenow, S. G. Stewart, F. M. Pfeffer, Asymmetric Induction in Domino Heck-aza-Michael Reactions, Tetrahedron Lett. 2012, 53, 1468-1471.

32. J. E. Rixson, T. Chaloner, C. H. Heath, L. F. Tietze, S. G. Stewart, The Development of Domino Reactions Incorporating the Heck Reaction: The Formation of N-Heterocycles, Eur. J. Org. Chem, 2012, 544-558.

31. M. Bradshaw, J. Zou, L. Byrne, K. S. Iyer, S. G. Stewart, Colin L. Raston, Pd(II) conjugated chitosan nanofibre mats for application in Heck cross-coupling reactions. Chem. Commun, 2011, 47, 12292-12294.

30. Y. S. Yee, S. Kampmann, K. A. Stubbs, B. W. Skelton, B. J. Kaskow, L. J. Abraham, S. G. Stewart, Novel Thalidomide Analogues with Potent NFB and TNF expression Inhibition, Med. Chem. Commun., 2011, 2, 1073-1078.

29.R. E. Martin, M. E. Polomska, L. T. Byrne, S. G. Stewart An intramolecular Tsuji-Trost reaction based approach to the synthesis of 6-methylene indolizidines, Tetrahedron Lett. 2011, 52, 4878-4881.

28. D. L. Priebbenow, F. M. Pfeffer, S. G. Stewart, A One-Pot, Three-Component Approach to Functionalised Tetrahydroisoquinolines Using Domino Heck–aza-Michael Reactions, Eur. J. Org. Chem, 2011, 1632-1635.

27.J. Zou, K. S. Iyer, S. G. Stewart, C. L. Raston, A Scalable synthesis of catalysts for the Mizoroki–Heck cross coupling reaction: palladium nanoparticles assembled in a polymeric nanosphere. New J. Chem., 2011, 35, 854-860.

26. N. A. Lengkeek, R. A. Boulos, A. J. McKinley, T. V. Riley, B. Martinac, S. G. Stewart, The Synthesis of Fluorescent DNA The Synthesis of Fluorescent DNA Intercalator Precursors through Efficient Multiple Heck Reactions Aust J Chem, 2011, 64, 316-323.

25. D. L Priebbenow, S. G Stewart, F. M. Pfeffer, A General Approach to N-Heterocyclic Scaffolds Using Domino Heck-aza-Michael Reactions, Org. Biomol. Chem., 2011, 1508-1515.

24.J. Zou, S. G. Stewart, C. L. Raston; K. S. Iyer, Surface oxygen triggered size change of palladium nano-crystals impedes catalytic efficacy, Chem. Commun., 2011, 47, 1803-1805.

23. J. Bajsa,; A. McCluskey,; C. P Gordon; S. G Stewart; T. A. Hill; R. Sahu,; S. O. Duke; B. L. Tekwani, The antiplasmodial activity of norcantharidin analogues that may act by protein phosphatase inhibition. Bioorg Med Chem Letts, 2010, 20, 6688-6695.

22. S. G. Stewart, C. J. Braun, M. E. Polomska, M. Karimi, L. J. Abraham, K. A. Stubbs, Efforts Toward Elucidating Thalidomides Molecular Target: An Expedient Synthesis of the First Thalidomide Biotin Analogue, Org. Biomol. Chem, 2010, 8, 4059 - 4062.

21. S. G. Stewart, E. L. Ghisalberti, B. W. Skelton, C. H. Heath, Formation and reactions of azepino[4,5-b]indoles: An unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones, Org. Biomol. Chem, 2010, 8, 3563.

20. H-d Xie, L. A. Ho, M. S. Truelove, B. Corry, S. G. Stewart, Fluorescent Triphenyl Substituted Maleimide Derivatives: Synthesis, Spectroscopy and Quantum Chemical Calculations, J Fluoresc, 2010, 20, 1077–1085.

19.D. L. Priebbenow, L. C. Henderson, F. M. Pfeffer, S. G. Stewart, Domino Heck-aza-Michael reactions; efficient access to 1-substituted tetrahydro-β-carbolines, J. Org. Chem. 2010, 1787-1790.

18.S. G. Stewart, C. J. Braun, S-L. Ng, M. E. Polomska, M. Karimi, L. J. Abraham, New thalidomide analogues derived through Sonogashira or Suzuki reactions and their TNF expression inhibition profiles, Bioorg. Med. Chem. 2010, 18, 650-662.

17.S. G. Stewart, L. A. Ho, M. E. Polomska, A. T. Percival, G. C. T. Yeoh, The rapid evaluation of Antrodia camphorata natural products and derivatives in tumorigenic liver progenitor cells using a novel cell proliferation assay. ChemMedChem, 2009, 4, 1657.

16.S. G. Stewart, C. H. Heath, E. L. Ghisalberti, Domino or Single-Step Tsuji–Trost/Heck Reactions and their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems, Eur. J. Org. Chem, 2009, 1934.

15.T. A. Hill, S. G. Stewart, C. P. Gordon, S. P. Ackland, J. Gilbert, B. Sauer, J. A Sakoff, A. McCluskey, Norcantharidin Analogues: Synthesis, Anticancer Activity and Protein Phosphatase 1 and 2A Inhibition. ChemMedChem, 2008, 3, 1878.

14.W. M. Loke, J. M. Proudfoot, S. Stewart, A. J. McKinley, P. W. Needs, P. A. Kroon, J. M. Hodgson and K. D. Croft, Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: Lack of association between antioxidant and lipoxygenase inhibitory activity, Biochemical Pharmacology, 2008, 75, 1045.

13.S. G. Stewart, T. A. Hill, J. Gilbert, S. P. Ackland, J. A. Sakoff, A. McCluskey, Synthesis and biological evaluation of norcantharidin analogues: Towards PP1 selectivity. Bioorg. Med. Chem. 2007, 15, 7301.

12. S. G. Stewart, D. Spagnolo, M. E. Polomska, M. Sin, M. Karimi, L. J. Abraham, Synthesis and TNF expression inhibitory properties of new thalidomide analogues derived via Heck cross coupling. Bioorg. Med. Chem Letts. 2007, 17, 5819.

11.T. A. Hill, S. G. Stewart, S. P. Ackland, J. Gilbert, B. Sauer, J. A. Sakoff, A. McCluskey, Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation. Bioorg. Med. Chem. 2007, 15, 6126.

10. T. A. Hill, S. G. Stewart, B. Sauer, J. Gilbert, S. P. Ackland, J. A. Sakoff, A. McCluskey, Heterocyclic substituted cantharidin and norcantharidin analogues-synthesis, protein phosphatase (1 and 2A) inhibition and anticancer activity, Bioorg. Med. Chem. Letts, 2007, 17, 3392.

9.S. G. Stewart, M. E. Polomska, R. W. Lim,. A concise synthesis of maleic anhydride and maleimide natural products found in Antrodia camphorata, Tetrahedron Lett. 2007, 48, 2241.

8. A. McCluskey, S. K. Leitch, J. Garner, C. E. Caden, T. A. Hill, L. R. Odell, S. G. Stewart, BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols, Tetrahedron Lett. 2005, 46, 8229.

7.L. F. Tietze, S. G. Stewart, M. E. Polomska, Intramolecular Heck Reactions for the Synthesis of the Novel Antibiotic Mensacarcin, Eur. J. Org. Chem. 2005, 1752.

6. L. F. Tietze, S. G. Stewart, M. E. Polomska, A. Modi, A. Zeeck, Towards the Synthesis of the New Anticancer Agent Mensacarcin, Chemistry, Eur. J. 2004, 10, 5233.

5. M. G. Banwell, A. J. Edwards, M. D. McLeod, S. G. Stewart, A Chemoenzymatic Synthesis of the cis-Decalin Core Associated with the Novel Anti-Mitotic Agent Phomopsidin, Aust. J. Chem, 2004, 57,641.

4. M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle, Chemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors, Pure Appl. Chem, 2003, 75, 223.

3. M. G. Banwell, S. G. Stewart, Methyl 6-methoxy-1-oxoindan-4-carboxylate, Org. Prep. Proced. Int, 2001, 33, 177.

2. D. M. J. Wright, S. P. Baker, S. G. Stewart, P. J. Scammells, N6-(5,6-epoxynorbornyl)adenosine Analogs as A1 Adenosine Agonists, Bioorg. Med. Chem. Lett. 1998, 8, 3647.

1. M. G. Banwell, B. L. Flynn, S. G. Stewart, Selective Cleavage of Isopropyl Aryl Ethers by Aluminium Trichloride, J. Org. Chem. 1998, 63, 9139.
Funding received
Cancer Council of Western Australia
Alexander von-Humboldt Stiftung/Foundation
Ada Bartholomew Medical Research Trust Grant
School of Medicine, Dentistry and Health
UWA Priming Grant
Australian Institute of Nuclear Science and Engineering
NH&MRC
Memberships
2009-current Chair, Synthetic and Organic Group (WA-RACI)
2007-current Royal Australian Chemistry Institute Western Australian Committee Member
2004-current Australian Alexander Von Humboldt Society
2005-current Royal Australian Chemistry Institute Member
2006-2008 Exam and course reviewer for Taylors Teaching College
Honours and awards
2017 Kyoto University Foundation Invitation Fellowship for Research
2013 Japan Society for the Promotion of Science (JSPS),
Fellowship (Long Term)
2012 Tasmanian Alkaloids Lectureship
2010 The Athel Beckwith Lectureship for newly Appointed Staff
2010 Return Alexander von Humboldt Fellowship
2002-2004 Alexander von Humboldt Fellowship
Patents
1. Antimicrobial compounds, A. J. Mckinley; T. V. Riley; N. Lengkeek; S. Stewart; R. Boulos, PCT Int. Appl. (2011), WO 2011075766 A1 20110630.
Teaching
CHEM3306 Modern Organic Synthesis (Course Coordinator)
CHEM3305 Biological Chemistry (Course Coordinator)
CHEM1102 Organic Chemistry (Course Coordinator)
New and noteworthy
Postgraduate Students
(Current)
Kieran Jones: Nickel Catalysis and Natural Product Synthesis.
Jeremy Duczynski: Applications of Nanoparticles and small reagent synthesis/ (with Dr B Fuller)
Dennis Power: Imine coupling under Nickel catalysis and Natural product synthesis.
James Rixson: The Synthesis and Biological Evaluation of Anthrapyranone Antitumour Antibiotics (with Dr Kersten M. Gericke)
Nikki Man: The Synthesis and Biological Assessment of Novel Antibacterial Agents (with Prof Allan McKinley)

Past Students (Current Position)
Charles Heath (CSRIO)
Daniel Priebbenow (Prof.C.Bolm,Aachen University)
Jianli Zou (Franklin Kim, iCeMS, Kyoto University)
Sing Yee Yeung (Monash University)
Lien Phan (NMI)
Daniel Spagnolo (Worley Parsons)
Rou Wei Lim (National University Singapore)
Melvin Sin
Sze-Ling Ng
Steffen Meyer (Prof. Dr. Franc Meyer, Uni Goettingen)
Muhammad Khidir
Carlos Braun (Impex)
Thomas Chaloner (UWA, Medicine)
Louisa Ho (Dr Keith Stubbs, UWA)
Sven Kampmann (Epichem)
Current projects
Small Alkyne Fungal Metabolite Synthesis

Pyrrolesesquiterpene Natural Product Synthesis
Synthesis of Thalidomide Derivatives

Natural Product Synthesis Utilising Palladium Catalysis

Synthesis of Maleic Anhydride and Maleimide Natural Products Found in Antrodia camphorata

Nickel Catalysis in modern organic synthesis

The preperation of anthrapyranone natural products as highly active antimicrobial and anticancer agents


Collaborators

A/Professor Lawrie Abraham, Biochemistry and Molecular Biology, UWA
Professor George Yeoh, Biochemistry and Molecular Biology, UWA
Professor Lutz F Tietze, Universität Göttingen
Frederick Pfeffer, School of Biological and Chemical Sciences, Deakin University
Dr. Kersten Gericke, Bayer Schering Pharma AG

Research profile
Research profile and publications
 

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Last updated:
Tuesday, 3 November, 2015 2:39 PM